Acetic Acid → 1-(4-Boc-aminobutyl)piperazine

HRID 1097298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097298
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[C:25]([O:24][C:22](=[O:23])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:28])([CH3:26])[CH3:27]

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 59708788HCID 59708788, Verbindung

Produkt 1

HCID 41346911-(4-Boc-aminobutyl)piperazineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(4-tert-butoxycarbonylaminobutyl)piperazine-1-carboxylic acid benzyl ester (16) (3.26 g, 8.33 mmol), acetic acid (0.5 mL), and palladium hydroxide on carbon (60% wet, 0.98 g) in methanol (15 mL) was stirred under atmospheric hydrogen for 16 h. The catalyst was removed by suction filtration over Celite. The filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using concentrated ammonium hydroxide/methanol/dichloromethane to give 17 as a yellow oil (1.94 g, 91% yield): 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.53 (m, 4H), 2.35 (m, 6H), 2.45 (br, 1H), 2.94 (t, 4H), 3.12 (m, 2H), 5.32 (br, 1H); ESI MS m/z 258 [C13H27N3O2+H]+.

Aufarbeitung

  1. customThe catalyst was removed by suction filtration over Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by Biotage silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-113925ec462a4b68b1396b0c3646ebc4
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143256B2

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